but before I go…

“Had I known Josh’s blog was going to get so big, I never would’ve allowed him to do it.”

– my old boss

I’ve spent the first half of my life being underestimated. It used to bother me, now I use it to my advantage – they never see me coming. And god help the poor soul who ever tells me that I can’t do something. Oh PLEASE tell me that so I can watch the horror and panic on your face when I come out of nowhere and do it better than you.

I’ve also spent the first half of my life rebelling. There are rules that were made to keep order and protect people, these are the rules I respect as a citizen and a family man. But then there are rules that have outlived their usefulness or only exist to protect someone else’s entrenched interest or personal fiefdom. These make me want to smash my guitar and kick an amp off the stage.

People ask me where my confidence and aura of authority come from. Sometimes they assume that it must be arrogance but let me assure you that I am my own harshest critic. If self-deprecation were an Olympic sport, I’d be the prepubescent Soviet gymnast girl who’s been pumped full of hormones and will be shot out back after the event.

No, I think the assuredness comes from somewhere deeper and darker. From having seen too much. From having been used too roughly by those I believed in. From having watched character flaws become fatal to those I’ve thought of as role models for a time.

Finding out that Santa Claus isn’t real pales in comparison to the heartbreak that comes when you realize that your mentor is a fake or that your parents aren’t perfect.

I remember being 17 years old without a care in the world in 1994. School came easily to me and so did getting girls. I was middle class, had a million friends and was headed to the University of Maryland the following fall. And then my idyllic world was shattered.

“Let’s follow him,” my younger brother said, handing me the keys to my Jeep. “Dad just said some bullshit about going to watch a game. There are no games on, let’s follow him.”

We are driving west on the Northern State Parkway three car lengths behind my father on a summer afternoon so bright I have the driver’s side sun visor down. My brother is fiddling with the radio, I am trying to remember all the tricks from the movies to remain out of sight as I tail the perp.

Exit into Westbury, a right at the light. He’s pulling over in a residential neighborhood. I ease off the gas and find a spot to pull over 50 yards behind. A woman comes out of a house to greet my father as he clicks the car lock on his keychain. I have never seen her before. They embrace on the front lawn. I put the car in reverse and drive backwards to the end of the block, I can’t bear to turn around.

I am back on the parkway headed home. I’m fighting a tear back so my brother doesn’t see it. I realize later that it won’t matter. My brother and I are two very different people. He does not get sad, he gets angry. The lesson he takes from this episode at the age of 14 is that it’s every man for himself in this world, that it’s time to look out for Number 1.

My own takeaway from the eventual divorce is somewhat sadder. A switch is flipped. All the heroes I worshiped in real life and in my imagination become dead to me. The comic books go into boxes that will sit in my mother’s garage forever and to this day. The sports and movie posters come off the wall and the little seedling of rebellion inside of me explodes through the soil and becomes the implacable oak that will permanently mark my personality, even now in adulthood.

When your dad can’t be your hero anymore, is there anything left to believe in?

***

15 years of raging against the machine and clawing my way past liars, schemers, frauds and idiots will follow this moment. I will make big mistakes and work too hard with too little to show for it. I will be loyal to the wrong people and schooled in the wrong ideologies. At times I will hate the world and my place in it. Fighting and fighting and fighting some more.

***

Fast-forward to now.

To quote Billy Joel, “things are okay with me these days…”

I married the first girl I ever fell in love with, my high school sweetheart.

We own the house we’re raising our children in with no mortgage.

I have the job that I want and I’m working with the people I want to work with. I have a book full of clients I truly care about and they appreciate my work on their behalf.

Every month hundreds of thousands of people read and hear what I have to say about the market, which is mind-blowing if you think about it.

That little brother of mine, whom I was worried would disappear into a selfish hedge maze of his own design, just told me last week that he’s about to be a father for the first time – and I get to be Uncle Josh!

So my confidence comes from experience and from knowing how this all works. Yes, all of it – each episode of joy or pain being a mere variation on a past one.

Maybe my friend James Altucher is right when he says that “most things don’t work out“. But what if most things don’t work out but the big things do? What if the things that don’t work out, that bring you to your knees, only fail so that your successes can actually mean something?

It’s easier to bear your past misfortunes once you’ve come to accept that they’ve made you into the person you’ve become and are becoming.

So yes, being perpetually underestimated and bristling against the antiquated constraints that keep old men in power can be an exhausting way to go through life. But I’ve finally found a way to make it all pay off.

Starting tomorrow I’m taking a week off from my duties here at The Reformed Broker. I have to finish the manuscript for my book, Backstage Wall Street, so I can submit it to McGraw-Hill. The book will be as punk-rock rebellious as anything ever written by someone working in finance.

I will be radio silent until next Friday but I’ve lined up a special guest blogger for each day of my absence. You may not miss me this week but I will miss you guys insufferably.

See ya soon,

Josh

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